1-(2,5-二甲基-4-苯基呋喃-3-基)乙酮 | 88484-88-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2,5-二甲基-4-苯基呋喃-3-基)乙酮
• 英文名称: 1-(2,5-Dimethyl-4-phenylfuran-3-yl)-1-ethanone
• 英文别名: 1-(2,5-dimethyl-4-phenylfuran-3-yl)ethan-1-one；1-(2,5-dimethyl-4-phenylfuran-3-yl)ethanone；2,5-dimethyl-3-acetyl-4-phenylfuran；2,5-dimethyl-4-phenyl-3-acetylfuran；3-Acetyl-2,5-dimethyl-4-phenylfuran；Ethanone, 1-(2,5-dimethyl-4-phenyl-3-furanyl)-
• CAS: 88484-88-2
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: VSQSIQJUGGFEQS-UHFFFAOYSA-N

物化性质

• 沸点：
  314.7±42.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2,5-二甲基-4-苯基呋喃-3-基)乙酮 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 10.0~25.0 ℃ 、245.15 kPa 条件下， 反应 3.0h， 生成 Methyl 5(6)-<3-(2,5-dimethyl-4-phenylfur-3-yl)-3-oxopropyl>benzimidazole-2-carbamate
  参考文献：
  名称：

  Niwas, Shri; Kumar, Shiv; Bhaduri, A. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 747 - 753

  摘要：

  DOI：
• 作为产物：
  描述：

  5,5-Diacetyl-3-methyl-4-phenyl-2-isoxazoline 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 1-(2,5-二甲基-4-苯基呋喃-3-基)乙酮
  参考文献：
  名称：

  Yuan, Chengye; Li, Chaozhong, Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 78, # 1-4, p. 47 - 54

  摘要：

  DOI：

文献信息

• Condensation of propargylic alcohols with 1,3-dicarbonyl compounds and 4-hydroxycoumarins in ionic liquids (ILs)
  作者：Gopalakrishnan Aridoss、Kenneth K. Laali

  DOI：10.1016/j.tetlet.2011.10.021

  日期：2011.12

  Propargylic alcohols are activated toward 1,3-diketones by Lewis or Brønsted acidic ionic liquids (ILs) without an added catalyst, but significantly better conversions are achieved with metallic triflates [in particular Sc(OTf)3 and Ln(OTf)3] and bismuth nitrate in imidazolium ILs. The scope of this condensation reaction was investigated with a variety of propargylic alcohols and a host of acyclic

  在没有添加催化剂的情况下，路易斯或布朗斯台德酸性离子液体（ILs）将炔丙醇活化为1,3-二酮，但是金属三氟甲磺酸酯[特别是Sc（OTf）3和Ln（OTf）3 ]可以实现明显更好的转化咪唑类ILs中的硝酸铋。用各种炔丙醇和许多无环和环状二羰基化合物研究了这种缩合反应的范围。与炔丙基醇1b和1c与1，3-二酮2b和β-酮酸酯2c反应时观察到伴随的环异构化，产生四取代的呋喃。与炔丙醇1c取决于1，3-二羰基化合物的结构，观察到炔丙基化，环异构化或二烯酮形成。经证明，[BMIM] [PF 6 ] / Bi（NO 3）3 ·5H 2 O体系对于4-羟基香豆素的炔丙基化，乙烯基化和烷基化有效。IL的回收和重用是该方法的其他优点。
• Copper-Catalyzed Three-Component Reactions of α-Ketoaldehyde, 1,3-Dicarbonyl Compound, and Organic Boronic Acid in Water: A Route to 1,4-Diketones
  作者：Qi Xia、Xiang Li、Xi Fu、Yaxuan Zhou、Yanqing Peng、Jiayi Wang、Gonghua Song

  DOI：10.1021/acs.joc.1c01100

  日期：2021.7.16

  reaction of α-ketoaldehydes, 1,3-dicarbonyl compounds, and organic boronic acids catalyzed by CuO in water has been developed to give a wide range of products containing 1,3/1,4-diketones. The method has some advantages such as the use of readily available starting materials, wide substrate scopes, excellent yields, gram-scale synthesis, and mild reaction conditions.

  已开发出一种新型的 α-酮醛、1,3-二羰基化合物和有机硼酸在水中由 CuO 催化的三组分反应，可得到多种含有 1,3/1,4-二酮的产物。该方法具有原料易得、底物范围广、收率高、克级合成、反应条件温和等优点。
• A Novel Propargylation/Cycloisomerization Tandem Process Catalyzed by a Ruthenium(II)/Trifluoroacetic Acid System: One-Pot Entry to Fully Substituted Furans from Readily Available Secondary Propargylic Alcohols and 1,3-Dicarbonyl Compounds
  作者：Victorio Cadierno、José Gimeno、Noel Nebra

  DOI：10.1002/adsc.200600366

  日期：2007.2.5

  and highly efficient method for the preparation of tetrasubstituted furans starting from readily accessible propargylic alcohols and commercially available 1,3-dicarbonyl compounds has been developed. The process, which proceeds in a one-pot manner, involves the initial propargylation of the 1,3-dicarbonyl compound promoted by trifluoroacetic acid, and subsequent cycloisomerization of the resulting

  已经开发了一种从容易获得的炔丙醇和可商购的1，3-二羰基化合物开始制备四取代呋喃的简单高效的方法。该过程以一锅法进行，涉及由三氟乙酸促进的1,3-二羰基化合物的初始炔丙基化，以及随后由16电子烯丙基钌（II）催化的所得γ-酮炔的环异构化。复杂的[Ru（η 3 -2-C 3 H ^ 4 ME）（CO）（DPPF）] [的SbF 6 ]。
• Synthesis of Tetrasubstituted NH Pyrroles and Polysubstituted Furans via an Addition and Cyclization Strategy
  作者：Zheng-Hui Guan、Liang Li、Mi-Na Zhao、Zhi-Hui Ren、Jianli Li

  DOI：10.1055/s-0031-1289993

  日期：2012.2

  enamino esters with nitroolefins provides a straightforward and general method for the synthesis of tetrasubstituted NH pyrroles. This novel method tolerates a wide range of functionality, and allows for rapid elaboration of the nitroolefins into a variety of substituted pyrroles in good yields. Further, an efficient KOAc-promoted addition and cyclization protocol toward substituted furans has been

  FeCl 3催化的烯胺酯与硝基烯烃的加成和环化为合成四取代的NH吡咯提供了一种简单直接的通用方法。这种新颖的方法可耐受多种功能，并允许以高收率将硝基烯烃快速精制为各种取代的吡咯。此外，也已经描述了针对取代的呋喃的有效KOAc促进的加成和环化方案。 四取代的NH吡咯-多取代的呋喃-加成-环化
• Direct Synthesis of Highly Substituted Furans from Acyloins and Active Methylene Compounds Catalyzed by Bismuth Triflate
  作者：Kimihiro Komeyama、Yuuki Ohama、Ken Takaki

  DOI：10.1246/cl.2011.1103

  日期：2011.10.5

  Bi(OTf)3 was found to be an effective catalyst for a tandem condensation/cyclization of acyloins and β-diketones or β-keto esters to afford highly substituted furans in good yields.

  Bi(OTf)3 被发现是一种有效的催化剂，可用于 acyloins 和 β-二酮或 β-酮酯的串联缩合/环化，以良好的收率提供高度取代的呋喃。